The smartest founders in managed IT show how they actually build.
No vendors reading scripts. Operators opening their books: pricing changes that worked, niches they own, near-death moments, and the numbers behind all of it. Hosted by Alexej Pikovsky.
Six Private Equity Offers a Week, and He Sold to His Staff Instead
Eric Rieger turned down six private equity offers a week and sold WEBIT Services to his employees instead, with the real numbers on what an employee stock ownership plan (ESOP) costs to set up and run.
Every episode, one playbook taken apart.
Each episode gets its own page with show notes and timestamped chapters. Send anyone a link and they land on the exact story.
Six Private Equity Offers a Week, and He Sold to His Staff Instead
He Ran IT Inside the Agencies. Then He Started Serving Them.
The MSP Built for Clients Nobody Can Standardise
The $500K Wire That Turns an MSP Into the Defendant
Why a Three Person Fund Gets Billed for Ten Seats
Your Gross Margin Is Misreported and Misunderstood
Stop Selling to the Office Manager: How an MSP Owner Became the Board's vCISO
You Can't Take AI to Court: Why Compliance Still Needs Humans
Buying MSPs at 1-2x Profit While the Market Pays 5-8x
The Google-Only MSP That Turned Its Audit Into a SaaS
140 Clients, No Employees: How a Solo MSP Does It
The Fire Round.
Eight questions, the same every episode, answered fast. It's where the honest answers live. Compare how every guest calls cloud vs on-prem, or which client they should have fired sooner.
EVERY GUEST · EVERY EPISODE · NO PREP ALLOWED
- One tool you couldn't run your MSP without?
- Most overrated thing in the MSP world right now?
- Most underrated?
- The client you should have fired sooner than you did?
- Best money you've spent on the business under $500?
- Cloud or on-prem in five years, in one word?
- One piece of advice for someone starting a solo MSP tomorrow?
- Finish this: the MSPs that survive the next five years will be the ones that...
Run an MSP with a story worth telling?
A niche you own. A pricing change that worked. A near-death moment you survived. Just the story of how you actually built it.
Pitch your story →01 · REAL NUMBERS, NOT RANGES
02 · A DECISION OTHERS AVOID
03 · THE MISTAKE THAT TAUGHT YOU
04 · HOW YOU ACTUALLY BUILT IT
Alexej Pikovsky asks the questions vendors won't.
Alexej runs growth inside a national MSP and has spent a decade buying, building, and exiting companies. He hosts Play It Smart to learn how the best operators in managed IT, security, and AI actually run their businesses, and to make that knowledge public.
The rule of the show: guests bring numbers, the host brings questions.
The research behind the questions.
Every episode stands on research. The full library lives on this site's Insights and on NUOPTIMA, the growth agency behind the show's production.